Aryl sulfonyl amino carbonyl triazole based selective herbicides

ABSTRACT

The invention relates to novel herbicidal synergistic active compound combinations which comprise firstly arylsulphonylaminocarbonyltriazolinones and secondly herbicidally active compounds and/or safeners listed in the description, and which can be used with particularly good results for the selective control of weeds in various crops of useful plants.

The invention relates to novel herbicidal synergistic active compoundcombinations which comprise firstly knownarylsulphonylaminocarbonyltriazolinones and secondly known herbicidallyactive compounds, and which can be used with particularly good resultsfor the selective control of weeds in various crops of useful plants.

Arylsulphonylaminocarbonyltriazolinones, being broad-range herbicides,are the subject-matter of a series of patent applications (cf.EP-A-341489, EP-A-422469, EP-A-425948, EP-A-431291, EP-A-507171,EP-A-534266, WO-A-96/11188, WO-A-96/27590, WO-A-96/27591,WO-A-97/03056). However, under certain circumstances, the knownsulphonylaminocarbonyltriazolinones still have gaps with regard to theiraction.

A number of herbicidal active compound combinations based onarylsulphonylaminocarbonyltriazolinones have also been disclosed already(cf. WO-A-98/12923). Again, however, the properties of these activecompound combinations are not satisfactory in all respects.

Surprisingly, it has now been found that a number of known activecompounds from the group of the arylsulphonylaminocarbonyltriazolinones,used jointly with known herbicidally active compounds from variousclasses of substances, show pronounced synergistic effects with regardto the action against weeds and can be employed particularlyadvantageously as broad-range combination products for the selectivecontrol of weeds in crops of useful plants such as, for example, barley,maize, rice and wheat.

The invention provides selective herbicidal compositions, characterizedin that they comprise an effective amount of an active compoundcombination consisting of

(a) an arylsulphonylaminocarbonyltriazolinone of the general formula (I)

in which

-   R¹ represents hydrogen, hydroxyl, amino, alkylideneamino or    represents in each case optionally substituted alkyl, alkenyl,    alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, cycloalkyl,    cycloalkylalkyl, cycloalkylamino, aryl or arylalkyl,-   R² represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen or    represents in each case optionally substituted alkyl, alkoxy,    alkylthio, alkylamino, dialkylamino, alkenyl, alkinyl, alkenyloxy,    alkinyloxy, alkenylthio, alkinylthio, alkenylamino, alkinylamino,    cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino,    cycloalkylalkyl, aryl, aryloxy, arylthio, arylamino or arylalkyl,-   R³ represents nitro, cyano, halogen or represents in each case    optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl,    alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkenyl,    alkenyloxy, alkenylthio, alkenylamino, alkinyl, alkinyloxy,    alkinylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio,    cycloalkylamino, aryl, aryloxy, arylthio, arylsulphinyl,    arylsulphonyl or arylamino, and-   R⁴ represents hydrogen, nitro, cyano, halogen or represents in each    case optionally substituted alkyl, alkylcarbonyl, alkoxy,    alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl,    alkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkinyl,    alkinyloxy, alkinylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio,    cycloalkylamino, aryl, aryloxy, arylthio, arylsulphinyl,    arylsulphonyl or arylamino,    and/or a salt of a compound of the formula (I)    (“active compounds of group 1”) and

(b) one to three compounds from a second group of herbicides comprisingthe active compounds listed below:

5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid sodium salt(acifluorfen-sodium),4-amino-N-(1,1-dimethyl-ethyl)-4,5-dihydro-3-(1-methyl-ethyl)-5-oxo-1H-1,2,4-triazole-1-carboxamide(amicarbazone), 1H-1,2,4-triazol-3-amine (amitrole),2-[2,4-dichloro-5-(2-propinyloxy)-phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]-pyridin-3(2H)-one(azafenidin),N-(4,6-dimethoxy-pyrimidin-2-yl)-N′-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-ylsulphonyl]-urea(azimsulfuron),N-benzyl-2-(4-fluoro-3-trifluoromethyl-phenoxy)-butanamide(beflubutamid),N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzenamine (benfluralin),N-(4,6-dimethoxy-pyrimidin-2-yl)-N′-(2-methoxycarbonyl-phenylmethylsulphonyl)-urea(bensulfuron), methyl2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)phenoxy]methyl]-5-ethyl-phenoxy-propanoate(benzfendizone),3-(2-chloro-4-methylsulphonyl-benzoyl)-4-phenylthio-bicyclo-[3.2.1]-oct-3-en-2-one(benzobicyclon), [1,1-dimethyl-2-oxo-2-(2-propenyloxy) ]-ethyl2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-benzoate(butafenacil-allyl),2-(1-ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxo-butyl)-phenyl]-2-cyclohexen-1-one(butroxydim),N,N-diethyl-3-(2,4,6-trimethyl-phenylsulphonyl)-1H-1,2,4-triazole-1-carboxamide(cafenstrole),2-[1-[(3-chloro-2-propenyl)-oxy-imino]-propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-one(caloxydim, tepraloxydim),N-(4-chloro-6-methoxy-pyrimidin-2-yl)-N′-(2-ethoxycarbonyl-phenylsulphonyl)-urea(chlorimuron-ethyl), ethyl2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenyl]-2-propanoate(cinidon-ethyl),2-[1-[2-(4-chloro-phenoxy)-propoxyamino]butyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione(clefoxydim),(E,E)-(+)-2-[1-[[(3-chloro-2-propenyl)-oxy]-imino]-propyl]-3-hydroxy-2-cyclohexen-1-one(clethodim), 2-(1-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one(cycloxydim), butyl(R)-2-[4-(4-cyano-2-fluoro-phenoxy)-phenoxy]-propanoate(cyhalofop-butyl),N-(2,6-dichloro-phenyl)-5-ethoxy-7-fluoro-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide(diclosulam),2-[1-[(3,5-difluoro-phenyl)-amino-carbonyl-hydrazono]-ethyl]-pyridine-3-carboxylicacid (diflufenzopyr), S-(1-methyl-1-phenyl-ethyl)1-piperidine-carbothioate (dimepiperate),(S-)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide(dimethenamid-P),2-[2-(3-chloro-phenyl)-oxiranylmethyl]-2-ethyl-1H-indene-1,3(2H)-dione(epropodan), ethyl(R)-2-[4-(6-chloro-benzoxazol-2-yl-oxy)-phenoxy]-propanoate(fenoxaprop-(P)-ethyl),4-(2-chloro-phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide(fentrazamide),N-(2,6-difluoro-phenyl)-8-fluoro-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide(florasulam), butyl(R)-2-[4-(5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoate(fluazifop, -butyl, -P-butyl), i-propyl5-(4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-chloro-4-fluoro-benzoate(fluazolate),N-(4-fluorophenyl)-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)-acetamide(flufenacet), ethyl[2-chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluoromethyl-1(6H)-pyridazinyl)-phenoxy]-acetate(flufenpyr), 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propinyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3-dione(flumioxazin),3-chloro-4-chloromethyl-1-(3-trifluoromethyl-phenyl)-2-pyrrolidinone(fluorochloridone),5-(2-chloro-4-trifluoromethyl-phenoxy)-N-methylsulphonyl-2-nitro-benzamide(fomesafen), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulphonyl]-4-formylamino-N,N-dimethyl-benzamide(foramsulfuron),(R)-2-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoic acid (methyl ester, 2-ethoxy-ethyl ester, butyl ester)(haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-ureasodium salt (iodosulfuron-methyl-sodium),(4-chloro-2-methylsulphonyl-phenyl)-(5-cyclopropyl-isoxazol-4-yl)-methanone(isoxachlortole),(2-ethoxy-1-methyl-2-oxo-ethyl)-5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoate(lactofen), 2-(2-benzothiazolyloxy)-N-methyl-N-phenyl-acetamide(mefenacet), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulphonyl]-4-[[(methylsulphonyl)-amino]methyl]-benzoate (mesosulfuron),2-(4-methylsulphonyl-2-nitro-benzoyl)-1,3-cyclohexanedione (mesotrione),4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (metamitron),(S)-2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide(S-metolachlor), 4-dipropylamino-3,5-dinitro-benzenesulphonamide(oryzalin),3-[2,4-dichloro-5-(2-propinyloxy)-phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-one(oxadiargyl),3-[2,4-dichloro-5-(1-methyl-ethoxy)-phenyl]-5-(t-butyl)-1,3,4-oxadiazol-2(3H)-one(oxadiazon),3-[1-(3,5-dichloro-phenyl)-1-i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one(oxaziclomefone),2-chloro-1-(3-ethoxy-4-nitro-phenoxy)-4-trifluoromethyl-benzene(oxyfluorfen),2-(2,2-difluoro-ethoxy)-N-(5,8-dimethoxy[1,2,4]trizolo[1,5-c]pyrimidin-2-yl)-6-trifluoromethyl-benzenesulphonamide(penoxsulam),2-chloro-N-(2-ethoxy-ethyl)-N-(2-methyl-1-phenyl-2-propenyl)-acetamide(pethoxamid),1-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluoro-tetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]-phenyl]-methanesulphonamide (profluazol), N-(3,4-dichloro-phenyl)-propanamide(propanil),(R)-[2-[[(1-methyl-ethylidene)-amino]-oxy]-ethyl]-2-[4-(6-chloro-2-quinoxalinyloxy)-phenoxy]-propanoate (propaquizafop),2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-[(1-methyl-ethoxy)-methyl]-acetamide(propisochlor),1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]-pyridin-2-yl)-5-(methyl-2-propinylamino)-1H-pyrazole-4-carbonitrile(pyraclonil), 6-chloro-3-phenyl-4-pyridazin-4-ol (pyridatol),7-[(4,6-dimethoxy-2-pyrimidinyl)-thio]-3-methyl-1(3H)-isobenzofuranone(pyriftalid), methyl 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzoate(pyriminobac-methyl),2-chloro-6-(4,6-dimethoxy-pyrimidin-2-ylthio)-benzoic acid sodium salt(pyrithiobac-sodium), 3,7-dichloro-quinoline-8-carboxylic acid(quinchlorac), 2-[4-(6-chloro-2-quinoxalinyloxy)-phenoxy]-propanoic acid(ethyl ester, tetrahydro-2-furanyl-methyl ester) (quizalofop, -ethyl,-P-ethyl, -P-tefuryl),2-(1-ethoximinobutyl)-5-(2-ethylthiopropyl)-3-hydroxy-2-cyclohexen-1-one(sethoxydim), methyl2-difluoromethyl-5-(4,5-dihydro-thiazol-2-yl)-4-(2-methyl-propyl)-6-trifluoromethyl-pyridine-3-carboxylate(thiazopyr), (3,5,6-trichloro)-pyridin-2-yl-oxy-acetic acid (triclopyr),N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(2,2,2-trifluoro-ethoxy)-2-pyridinesulphonamidesodium salt (trifloxysulfuron),N-[4-dimethylamino-6-(2,2,2-trifluoro-ethoxy)-1,3,5-triazin-2-yl]-N′-(2-methoxycarbonyl-phenylsulphonyl)-urea(triflusulfuron-methyl), N-[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-3-(N-methyl-N-methylsulphonyl-amino)-2-pyridinesulphonamide(cf. WO-A-92/10660),2-(3,4-difluoro-phenoxy)-4-methyl-6-[(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)-oxy]-pyridine(cf. EP-A-937397, WO-A-98/04548),

(“active compounds of group 2”), and optionally

(c) a compound which improves crop plant compatibility, from the groupof compounds below:

4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67),1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one(dicyclonon, BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl—cf.also related compounds in EP-A-86750, EP-A-94349, EP-A-191736,EP-A-492366), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea(cumyluron), α-(cyanomethoximino)-phenylacetonitrile (cyometrinil),2,4-dichloro-phenoxy acetic acid (2,4-D),1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron),3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethylpiperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenyl acetamide (dichlormid),4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 andEP-A-346620), phenylmethyl2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine(furilazole, MON-13900), ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl—cf. also related compounds inWO-A-95/07897),diethyl-1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874),2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-naphthalicanhydride, α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile(oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide(PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), methyl1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf.also related compounds in EP-A-269806 and EP-A-333131), ethyl5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. alsorelated compounds in WO-A-91/08202), 1,3-dimethyl-but-1-yl5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinolin-8-oxy-acetate,ethyl 5-chloro-quninolin-8-oxy-acetate, allyl5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl5-chloro-quinolin-8-oxy-acetate, diethyl5-chloro-quinolin-8-oxy-malonate, diallyl5-chloro-quinolin-8-oxy-malonate, diethyl5-chloro-quinolin-8-oxy-malonate (cf. also related compounds inEP-A-582198), 2-(4-carboxy-chroman-4-yl)-acetic acid,3,3′-dimethyl-4-methoxy-benzophenone,1-bromo-4-chloromethylsulphonyl-benzene,N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide,N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropylaminocarbonyl)-benzenesulphonamide,N-cyclopropyl-4-[(2-methoxy-5-methyl-benzoyl)-amino-sulphonyl]-benzamide (cf. WO 99/66795),

(“active compounds of group 3”).

Preferred meanings of the radicals listed in formula (I) shown above areillustrated below.

-   R¹ preferably represents hydrogen, hydroxyl, amino,    C₂-C₆-alkylideneamino, represents in each case optionally cyano-,    halogen- or C₁-C₄-alkoxy-substituted alkyl, alkenyl, alkinyl,    alkoxy, alkenyloxy, alkylamino or dialkylamino having in each case    up to 6 carbon atoms, represents in each case optionally cyano-,    halogen- or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkylalkyl or    cycloalkylamino having in each case 3 to 6 carbon atoms in the    cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl    moiety, or represents in each case optionally cyano-, nitro-,    halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or    C₁-C₄-halogenoalkoxy-substituted phenyl or phenyl-C₁-C₄-alkyl.-   R² preferably represents hydrogen, hydroxyl, mercapto, amino, cyano,    halogen, represents in each case optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino,    dialkylamino, alkenyl, alkinyl, alkenyloxy, alkinyloxy, alkenylthio,    alkinylthio, alkenylamino or alkinylamino having in each case up to    6 carbon atoms, represents in each case optionally cyano-, halogen-    or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkyloxy,    cycloalkylthio, cycloalkylamino or cycloalkylalkyl having in each    case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1    to 4 carbon atoms in the alkyl moiety, or represents in each case    optionally cyano-, nitro-, halogen-, C₁-C₄-alkyl-,    C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or    C₁-C₄-halogenoalkoxy-substituted phenyl, phenoxy, phenylthio,    phenylamino or phenyl-C₁-C₄-alkyl.-   R³ preferably represents nitro, cyano, halogen, represents in each    case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,    alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl,    alkylsulphonyl, alkylamino, alkenyl, alkenyloxy, alkenylthio,    alkenylamino, alkinyl, alkinyloxy, alkinylthio having in each case    up to 6 carbon atoms, represents in each case optionally cyano-,    halogen- or C₁-C₄-alkyl-substituted cycloalkyl, cycloalkyloxy,    cycloalkylthio, cycloalkylamino having in each case 3 to 6 carbon    atoms in the cycloalkyl groups, or represents in each case    optionally cyano-, nitro-, halogen-, C₁-C₄-alkyl-,    C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-or    C₁-C₄-halogenoalkoxy-substituted phenyl, phenoxy, phenylthio,    phenylsulphinyl, phenylsulphonyl or phenylamino.-   R⁴ preferably represents hydrogen, nitro, cyano, halogen, represents    in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted    alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio,    alkylsulphinyl, alkylsulphonyl, alkylamino, alkenyl, alkenyloxy,    alkenylthio, alkenylamino, alkinyl, alkinyloxy or alkinylthio having    in each case up to 6 carbon atoms, represents in each case    optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl,    cycloalkyloxy, cycloalkylthio, cycloalkylamino having in each case 3    to 6 carbon atoms in the cycloalkyl groups, or represents in each    case optionally cyano-, nitro-, halogen-, C₁-C₄-alkyl-,    C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- or    C₁-C₄-halogenoalkoxy-substituted phenyl, phenoxy, phenylthio,    phenylsulphinyl, phenylsulphonyl or phenylamino.-   R¹ particularly preferably represents hydrogen, amino, represents in    each case optionally cyano-, fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or    t-butyl, ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl,    methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,    propenyloxy, butenyloxy, methylamino, ethylamino, n- or    i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or    diethylamino, represents in each case optionally cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,    cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,    cyclopropylamino, cyclobutylamino, cyclopentylamino or    cyclohexylamino, or represents in each case optionally cyano-,    nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or    i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-,    ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl or    benzyl.-   R² particularly preferably represents hydrogen, hydroxyl, mercapto,    amino, cyano, fluorine, chlorine, bromine, represents in each case    optionally cyano-, fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or    t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,    methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or    t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-,    s- or t-butylamino, dimethylamino, diethylamino, ethenyl, propenyl,    butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy,    propinyloxy, butinyloxy, propenylthio, butenylthio, propinylthio,    butinylthio, propenylamino, butenylamino, propinylamino or    butinylamino, represents in each case optionally cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy,    cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,    cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino,    cyclobutylamino, cyclopentylamino, cyclohexylamino,    cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or    cyclohexylmethyl, or represents in each case optionally cyano-,    nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or    i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-,    ethoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,    phenoxy, phenylthio, phenylamino or benzyl.-   R³ particularly preferably represents nitro, cyano, fluorine,    chlorine, bromine, represents in each case optionally cyano-,    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or    i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or    t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,    methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or    t-butylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-,    i-, s- or t-butylamino, ethenyl, propenyl, butenyl, propenyloxy,    butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino,    ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyl-thio    or butinylthio, represents in each case optionally cyano-,    fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or    i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,    cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,    cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,    cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino    or cyclohexylamino, or represents in each case optionally cyano-,    nitro-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or    i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-,    ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-    or trifluoromethoxy-substituted phenyl, phenoxy, phenylthio,    phenylsulphinyl, phenylsulphonyl or phenylamino.-   R⁴ particularly preferably represents hydrogen, nitro, cyano,    fluorine, chlorine, bromine, represents in each case optionally    cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n-    or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or    t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,    methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or    t-butylthio, methylsulphinyl, ethylsulphinyl, n- or    i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or    i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-,    i-, s- or t-butylamino, ethenyl, propenyl, butenyl, propenyloxy,    butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino,    ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylthio or    butinylthio, represents in each case optionally cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy,    cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,    cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino,    cyclobutylamino, cyclopentylamino or cyclohexylamino, or represents    in each case optionally cyano-, nitro-, fluorine-, chlorine-,    bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-,    methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenoxy,    phenylthio, phenylsulphinyl, phenylsulphonyl or phenylamino.-   R¹ very particularly preferably represents hydrogen, amino,    represents in each case optionally fluorine-, chlorine-, methoxy- or    ethoxy-substituted methyl, ethyl, n- or i-propyl, ethenyl, propenyl,    ethinyl, propinyl, methoxy, ethoxy, methylamino or ethylamino,    represents dimethylamino, or represents in each case optionally    fluorine-, chlorine- or methyl-substituted cyclopropyl.-   R² very particularly preferably represents hydrogen, chlorine,    bromine, represents in each case optionally fluorine-, chlorine-,    methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-    or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio,    n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino,    dimethylamino, diethylamino, ethenyl, propenyl, butenyl, ethinyl,    propinyl, butinyl, propenyloxy, butenyloxy, propinyloxy, butinyloxy,    propenylthio, butenylthio, propinylthio, butinylthio, propenylamino,    butenylamino, propinylamino or butinylamino, or represents in each    case optionally fluorine-, chlorine- or methyl-substituted    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy,    cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio,    cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino,    cyclobutylamino, cyclopentylamino, cyclohexylamino,    cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or    cyclohexylmethyl.-   R³ very particularly preferably represents nitro, cyano, fluorine,    chlorine, bromine, represents in each case optionally fluorine-,    chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or    i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,    ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n-    or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or    ethylsulphonyl, represents in each case optionally fluorine-,    chlorine- or methyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,    cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio,    cyclopentylthio or cyclohexylthio, or represents in each case    optionally cyano-, nitro-, fluorine-, chlorine-, bromine-, methyl-,    ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-,    methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or    trifluoromethoxy-substituted phenyl, phenoxy, phenylthio,    phenylsulphinyl or phenylsulphonyl.-   R⁴ very particularly preferably represents hydrogen, nitro, cyano,    fluorine, chlorine, bromine, or represents in each case optionally    fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,    n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,    ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n-    or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or    ethylsulphonyl.

In place of the pure active compounds of the formula (I), it is alsopossible to use salts of the compounds of the formula (1) with metalsand/or with basic nitrogen compounds in the active compound combinationsaccording to the invention.

Preference is given here to salts of the compounds of the formula (I)with alkali metals, such as, for example, lithium, sodium, potassium,rubidium or caesium, very particularly preferably with sodium orpotassium, with alkaline earth metals, such as, for example, magnesium,calcium or barium, very particularly preferably with calcium, or withearth metals, such as, for example, aluminium.

Preference is furthermore given to salts of the compounds of the formula(I) with ammonia, with C₁-C₆-alkyl-amines, such as, for example, withmethylamine, ethylamine, n- or i-propylamine, n-, i-, s- ort-butylamine, n-, i-, s- or t-pentylamine, with di-(C₁-C₆-alkyl)-amines,such as, for example, dimethylamine, diethylamine, dipropylamine,diisopropylamine, dibutylamine, diisobutylamine, di-s-butylamine,dipentylamine, diisopentylamine, di-s-pentylamine and dihexylamine, withtri-(C₁-C₄-alkyl)-amines, such as, for example, trimethylamine,triethylamine, tripropylamine, tributylamine andN-ethyl-diisopropylamine, with C₃-C₆-cycloalkyl-amines, such as, forexample, cyclopentylamine or cyclohexylamine, withdi-(C₃-C₆-cycloalkyl)-amines, such as, for example, dicyclopentylamineor dicyclohexylamine, with N-C₁-C₄-alkyl-C₃-C₆-cycloalkylamines, suchas, for example, N-methyl-cyclopentylamine, N-ethyl-cyclopentylamine,N-methyl-cyclohexylamine or N-ethyl-cyclohexylamine, withN,N-di-(C₁-C₄-alkyl)-C₃-C₆-cycloalkyl-amines, such as, for example,N,N-dimethyl-cyclopentylamine, N,N-diethyl-cyclopentylamine,N,N-dimethyl-cyclohexylamine or N,N-diethyl-cyclohexylamine, withN-C₁-C₄-alkyl-di-(C₃-C₆-cycloalkyl)-amines, such as, for example,N-methyl-dicyclopentylamine, N-ethyl-dicyclopentylamine,N-methyl-dicyclohexylamine or N-ethyl-dicyclohexylamine, withphenyl-C₁-C₄-alkyl-amines, such as, for example, benzylamine,1-phenyl-ethylamine or 2-phenyl-ethylamine, withN-C₁-C₄-alkyl-phenyl-C₁-C₄-alkyl-amines, such as, for example,N-methyl-benzylamine or N-ethyl-benzylamine, or withN,N-di-(C₁-C₄-alkyl)-phenyl-C₁-C₄-alkyl-amines, such as, for example,N,N-dimethyl-benzylamine or N,N-diethyl-benzylamine, or with optionallyfused and/or C₁-C₄-alkyl-substituted azines, such as, for example,pyridine, quinoline, 2-methyl-pyridine, 3-methyl-pyridine,4-methyl-pyridine, 2,4-dimethyl-pyridine, 2,5-dimethyl-pyridine,2,6-dimethyl-pyridine or 5-ethyl-2-methyl-pyridine.

Basic compounds which may be mentioned as being suitable for preparingthe salts of the compounds of the formula (I) that can be used accordingto the invention are: alkali metal or alkaline earth metal acetates,amides, carbonates, bicarbonates, hydrides, hydroxides or alkamolates,such as, for example, sodium acetate, potassium acetate or calciumacetate, lithium amide, sodium amide, potassium amide or calcium amide,sodium carbonate, potassium carbonate or calcium carbonate, sodiumbicarbonate, potassium bicarbonate or calcium bicarbonate, lithiumhydride, sodium hydride, potassium hydride or calcium hydride, lithiumhydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide,sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxideor potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- ort-butoxide.

Examples which may be mentioned for the compounds of the formula (I) tobe used as mixing partners according to the invention are:

2-(2-chloro-phenylsulphonylaminocarbonyl)-,2-(2-bromo-phenylsulphonylaminocarbonyl)-,2-(2-methyl-phenylsulphonylaminocarbonyl)-,2-(2-ethyl-phenylsulphonylaminocarbonyl)-,2-(2-n-propyl-phenylsulphonylaminocarbonyl)-,2-(2-i-propyl-phenylsulphonylaminocarbonyl)-,2-(2-trifluoromethyl-phenylsulphonylaminocarbonyl)-,2-(2-methoxy-phenylsulphonylaminocarbonyl)-,2-(2-ethoxy-phenylsulphonylaminocarbonyl)-,2-(2-n-propoxy-phenylsulphonylaminocarbonyl)-,2-(2-i-propoxy-phenylsulphonylaminocarbonyl)-,2-(2-difluoromethoxy-phenylsulphonylaminocarbonyl)-,2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-,2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-,2-(2-ethoxycarbonyl-phenylsulphonylaminocarbonyl)-,2-(2-n-propoxycarbonyl-phenylsulphonylaminocarbonyl)-,2-(2-i-propoxycarbonyl-phenylsulphonylaminocarbonyl)- and2-(2-chloro-6-methyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methyl-5-ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methyl-5-n-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methyl-5-i-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methyl-5-trifluoroethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methyl-5-ethylthio-2,4-dihydro-3 H-1,2,4-triazol-3 -one-4-methoxy-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-methoxy-5-n-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-cyclopropyl-5-ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-cyclopropyl-5-n-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-4-cyclopropyl-5-i-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and-4-cyclopropyl-5-trifluoroethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one andthe sodium and potassium salts of these compounds.

The compounds2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(I-1, procarbazone or propoxycarbazone) and2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(I-2, flucarbazone) and their sodium salts—(I-1-Na salt,procarbazone-sodium or propoxycarbazone-sodium), (I-2-Na salt,flucarbazone-sodium)—may be particularly emphasized as mixing componentsof the formula (I).

The compounds of the formula (I) are described in the patentapplications and patents mentioned above.

According to their chemical structure, the active compounds of group 2can be assigned to the following classes of active compounds:

amides (for example beflubutamid, propanil), arylheterocycles (forexample azafenidin, benzfendizone, butafenacil-allyl, cinidon-ethyl,fluazolate, flumioxazin, oxadiazon, oxadiargyl, profluazol,pyraflufen-ethyl, pyridatol,4-[4,5-dihydro-4-methyl-5-oxo-(3-trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulphonyl)amino]-5-fluoro-benzenecarbothioamide),aryloxyphenoxypropionates (for example cyhalofop-butyl,fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl,quizalofop-P-ethyl), carboxylic acid derivatives (for exampletriclopyr), chloroacetamides (for example dimethenamid-P, S-metolachlor,propisochlor), cyclohexanediones (for example butroxydim, clefoxydim,cycloxydim, sethoxydim), dinitroanilines (for example benfluralin,oryzalin), diphenyl ethers (for example acifluorfen-sodium, fomesafen,lactofen, oxyfluorfen), isoxazoles (for example isoxachlortole),oxyacetamides (for example mefenacet), pyridines (for examplethiazopyr), pyrimidinyl(thio)benzoates (for example pyribenzoxim,pyriminobac-methyl, pyrithiobac-sodium), sulphonylureas (for exampleazimsulfuron, bensulfuron, chloroimuron-ethyl, foramsulfuron,iodosulfuron-methyl-sodium, trifloxysulfuron, triflusulfuron-methyl),tetrazolinones (for example fentrazamide), thiocarbamates (for exampledimepiperate), triazinones (for example metamitron), triazoles (forexample amitrole), triazolopyrimidines (for example diclosulam,florasulam), triketones (for example mesotrione).

The following may be particularly emphasized as mixing components fromamongst the active compounds of group 2:

amicarbazone, beflubutamid, cinidon-ethyl, fenoxaprop-P-ethyl,florasulam, fluazolate, flufenacet, iodosulfuron-methyl-sodium.

From this group, amicarbazone is a mixing component of very particularinterest.

From this group, beflubutamid is a further mixing component of veryparticular interest.

From this group, cinidon-ethyl is a further mixing component of veryparticular interest.

From this group, fenoxaprop-P-ethyl is a further mixing component ofvery particular interest.

From this group, florasulam is a further mixing component of veryparticular interest.

From this group, fluazolate is a further mixing component of veryparticular interest.

From this group, flufenacet is a further mixing component of veryparticular interest.

From this group, iodosulfuron-methyl-sodium is a mixing component ofvery particular interest.

The compositions according to the invention preferably comprise one ortwo active compounds of group 1, one to three active compounds of group2 and optionally one active compound of group 3.

The compositions according to the invention comprise in particular oneactive compound of group 1, one or two active compounds of group 2 andoptionally one active compound of group 3.

The following may be particularly emphasized as mixing components fromamong the active compounds of group 3:

1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl) anddiethyl1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl) for improving the compatibility in cereals.

Examples of the active compound combinations according to the inventionwhich may be mentioned are:

flucarbazone-sodium+beflubutamid,flucarbazone-sodium+beflubutamid+mefenpyr-diethyl,flucarbazone-sodium+beflubutamid+cloquintocet-mexyl,flucarbazone-sodium+cinidon-ethyl,flucarbazone-sodium+cinidon-ethyl+mefenpyr-diethyl,flucarbazone-sodium+cinidon-ethyl+cloquintocet-mexyl,flucarbazone-sodium+fenoxaprop-P-ethyl,flucarbazone-sodium+fenoxaprop-P-ethyl+mefenpyr-diethyl,flucarbazone-sodium+fenoxaprop-P-ethyl+cloquintocet-mexyl,flucarbazone-sodium+florasulam,flucarbazone-sodium+florasulam+mefenpyr-diethyl,flucarbazone-sodium+florasulam+cloquintocet-mexyl,flucarbazone-sodium+flufenacet,flucarbazone-sodium+flufenacet+mefenpyr-diethyl,flucarbazone-sodium+flufenacet+cloquintocet-mexyl,flucarbazone-sodium+iodosulfuron-methyl-sodium,flucarbazone-sodium+iodosulfuron-methyl-sodium+mefenpyr-diethyl,flucarbazone-sodium+iodosulfuron-methyl-sodium+cloquintocet-mexyl.

Procarbazone-sodium+beflubutamid,procarbazone-sodium+beflubutamid+mefenpyr-diethyl,procarbazone-sodium+beflubutamid+cloquintocet-mexyl,procarbazone-sodium+cinidon-ethyl,procarbazone-sodium+cinidon-ethyl+mefenpyr-diethyl,procarbazone-sodium+cinidon-ethyl+cloquintocet-mexyl,procarbazone-sodium+fenoxaprop-P-ethyl,procarbazone-sodium+fenoxaprop-P-ethyl+mefenpyr-diethyl,procarbazone-sodium+fenoxaprop-P-ethyl+cloquintocet-mexyl,procarbazone-sodium+florasulam,procarbazone-sodium+florasulam+mefenpyr-diethyl,procarbazone-sodium+florasulam+cloquintocet-mexyl,procarbazone+iodosulfuron-methyl-sodium,procarbazone+iodosulfuron-methyl-sodium+mefenpyr-diethyl,procarbazone+iodosulfuron-methyl-sodium+cloquintocet-mexyl.

Surprisingly, it has now been found that the above-defined activecompound combinations of the arylsulphonylaminocarbonyltriazolinones ofthe formula (I) and the abovementioned active compounds of group 2exhibit a particularly high herbicidal activity combined with very gooduseful plant compatibility and can be used for the selective control ofmonocotyledonous and dicotyledonous weeds in a variety of crops, inparticular in wheat, but also in barley, and also for controllingmonocotyledonous and dicotyledonous weeds in the semi- and non-selectivefield. Surprisingly, the herbicidal activity of the active compoundcombinations according to the invention of compounds of theabovementioned groups 1 and 2 considerably exceeds the total of theactions of the individual active compounds.

Thus, not just a complementation of action but a synergistic effect ispresent which could not have been predicted. The novel active compoundcombinations are well tolerated in a variety of crops, also effectinggood control of weeds which are usually difficult to control. Thus, thenovel active compound combinations are a valuable addition to theherbicides.

The synergistic effect of the active compound combinations according tothe invention is particularly strongly pronounced in certainconcentration ratios. However, the weight ratios of the active compoundsin the active compound combinations may be varied within relatively wideranges. In general, from 0.01 to 1000 parts by weight, preferably from0.02 to 500 parts by weight and particularly preferably from 0.05 to 100parts by weight of active compound of group 2 are used per part byweight of active compound of the formula (I).

The following may be particularly emphasized as mixing components fromamongst the active compounds of group 3:

1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl),ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl)and diethyl1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl) for improving the compatibility in cereals, and4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67),1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid),3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148) and ethyl1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl) for improving the compatibility in maize.

It must be considered as surprising that, from amongst a large number ofknown safeners or antidotes capable of antagonizing the harmful effectof a herbicide on the crop plants, it is precisely the abovementionedcompounds of group 3 which are capable of almost completely neutralizingthe harmful effect, on the crop plants, of active compounds of theformula (I) and their salts, if appropriate also in combination with oneor more of the abovementioned active compounds of group 2, withoutadversely affecting the herbicidal efficacy towards the weeds.

The advantageous effect of the crop plant compatibility of the activecompound combinations according to the invention is likewiseparticularly strongly pronounced at certain concentration ratios.However, the weight ratios of the active compounds in the activecompound combinations can be varied within relatively wide ranges. Ingeneral, from 0.001 to 1000 parts by weight, preferably from 0.01 to 100parts by weight and particularly preferably from 0.1 to 10 parts byweight of active compound of group 3 are used per part by weight ofactive compound of the formula (I) or its mixtures with active compoundsof group 2.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (inclusive of naturally occurring crop plants).Crop plants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, inclusive of the transgenicplants and inclusive of the plant varieties protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all aerial and subterranean plant parts and organs of theplants such as shoot, leaf, flower and root, examples which may bementioned being leaves, needles, stalks, trunks, flowers, fruitingbodies, fruits, seeds, roots, tubers and rhizomes. The plant parts alsoinclude vegetative and generative propagation material, for examplecuttings, tubers, rhizomes, seedlings and seeds.

The treatment according to the invention of the plants and plant partswith the active compounds is carried out directly or by allowing thecompounds to act on their surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

Amongst the plants obtained by biotechnological and recombinant methods,or by combining these methods, plants which are emphasized are thosewhich tolerate so-called 4-HPPD, EPSP and/or PPO inhibitors, such as,for example, Acuron plants.

The active compounds according to the invention can be used, forexample, in the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compound combinations according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

The active compound combinations to be used in accordance with theinvention can be employed not only in conventional cultivation methods(suitably spaced row crops), in plantation crops (for examplegrapevines, fruit, citrus) and in industrial plants and railtracks, onpaths and squares, but also for stubble treatment and in the minimumtillage method. They are furthermore suitable as dessicants (haulmkilling in, for example, potatoes) or as defoliants (for example incotton). They are furthermore suitable for use on non-crop areas. Otherfields of application are nurseries, forests, grassland and theproduction of ornamentals.

The active compound combinations can be converted into the customaryformulations such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic materials impregnatedwith active compound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants and/or foam formers.

In the case of the use of water as an extender, organic solvents can,for example, also be used as cosolvents. The following are essentiallysuitable as liquid solvents: aromatics such as xylene, toluene, oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Solid carriers which are suitable are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic materials such as highly-dispersed silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, or else synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam formers are: for example nonionic and anionic emulsifierssuch as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, or else protein hydrolysates; suitabledispersants are: for example lignin sulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compounds, preferably between 0.5 and 90%.

The active compound combinations according to the invention aregenerally applied in the form of ready mixes. However, the activecompounds contained in the active compound combinations may also beapplied in the form of individual formulations which are mixed upon use,that is, in the form of tank mixes.

The novel active compound combinations, as such or in theirformulations, may furthermore also be used as a mixture with other knownherbicides, again with ready mixes or tank mixes being possible. Amixture with other known active compounds such as fungicides,insecticides, acaricides, nematicides, bird repellants, growthsubstances, plant nutrients and soil conditioners is also possible. Itmay furthermore be advantageous for specific applications, in particularfor the post-emergence method, to incorporate into the formulationsplant-tolerated mineral or vegetable oils (for example the commercialproduct “Oleo DuPont 11E”) or ammonium salts such as, for example,ammonium sulphate or ammonium thiocyanate, as further additives.

The novel active compound combinations can be used as such, in the formof their formulations or the use forms prepared from these formulationsby further dilution, such as ready-to-use solutions, suspensions,emulsions, powders, pastes and granules. Application is effected in thecustomary manner, for example by pouring, spraying, atomizing, dustingor broadcasting.

The active compound combinations according to the invention can beapplied before and after emergence of the plants, that is to say by thepre- and post-emergence method. They may also be incorporated into thesoil prior to sowing.

The good herbicidal action of the novel active compound combinations canbe seen from the examples which follow. While the individual activecompounds show weaknesses with regard to their herbicidal action, thecombinations all show a very good herbicidal action which exceeds asimple sum of actions.

A synergistic effect in herbicides is always present when the herbicidalaction of the active compound combination exceeds the action of theactive compounds when applied individually.

The expected action for a given combination of two herbicides can becalculated as follows (cf. COLBY, S. R.: “Calculating synergistic andantagonistic responses of herbicide combinations”, Weeds 15, pages20-22, 1967):

-   If-   X=% damage by herbicide A (active compound of the formula I) at an    application rate of p kg/ha-   and-   Y=% damage by herbicide B (active compound of the formula II) at an    application rate of q kg/ha-   and-   E=the expected damage of herbicides A+B at an application rate of    p+q kg/ha,-   then    E=X+Y−(X*Y/100).

If the actual damage exceeds the calculated value, the combination has asuperadditive effect, that is to say a synergistic effect.

The actual herbicidal activity of the active compound combinations ofthe present invention is higher than the calculated activity, i.e. thenovel active compound combinations act synergistically.

This is apparent in particular from the examples below.

USE EXAMPLES

Customary formulations of the active compounds tested were used.Procarbazone- and flucarbazone-sodium were used as 70 WG formulation.Fenoxaprop-P-ethyl was used in a mixture with mefenpyr-diethyl (75 g ofmefenpyr-diethyl/l) as Ralon® Super 69 EW. Cinidon-ethyl and florasulamand iodosufuron in a mixture with mefenpyr-diethyl were used in the formof the finished formulations Lotus® 200 EC, Primus® 50 SC and Hussar® 5WG (15% mefenpyr-diethyl), respectively. Amicarbazone was used as 70 WGformulation.

The required amount of active compound or formulation is dissolved in afew millilitres(2-3 ml) of the solvent (acetone or DMF), optionallyadmixed with an emulsifier (1 ml) and diluted with water to the desiredconcentration.

Mixtures are prepared by mixing a predetermined dissolved amount of thefirst active compound with the required amount of the second activecompound (and, if desired, with additional active compounds/formulationsor other ingredients), followed by dilution with water to the desiredconcentration.

In pre- and post-emergence experiments, the spray liquor is usuallyadmixed with a surfactant (Renex 36), at a concentration of 0.1%.

The amount of active compound or formulation is chosen such that thedesired application rate per ha is achieved.

Example B

Post-Emergence/Greenhouse

Test plants are grown under controlled conditions (temperature andlight). Once the plants have reached a height of 5 to 15 cm, the testcompound or the combination of test compounds is applied by sprayingsuch that the particular amounts of active compound desired are appliedper unit area. The concentration of the spray liquor is chosen so thatthe particular amounts of active compound desired are applied in 500 lof water/ha.

Following the spray application, the plant containers are kept in agreenhouse under constant light and temperature conditions.

After about 3 weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

-   0%=no damage (like untreated control)-   100%=total destruction/damage

Active compounds, application rates, test plants and results are shownin the tables below, the abbreviations used in the tables having thefollowing meanings:

-   a.i.=active ingredient=active compound

TABLE B-1 Application Alopecurus Alopecurus rate myosuroides myosuroidesg of ai/ha observed calculated* Procarbazone- 60 70 sodium 30 70 15 60Fenoxaprop-P- 30 0 ethyl 15 0 Procarbazone- 60 + 30 80 70 sodium + 30 +30 80 70 fenoxaprop-P- 15 + 30 80 60 ethyl 30 + 15 80 70 15 + 15 80 60Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-2 Application Bromus Bromus rate secalinus secalinus g of ai/haobserved calculated* Procarbazone- 15 80 sodium Fenoxaprop-P- 60 0 ethyl30 0 Procarbazone- 15 + 60 90 80 sodium + 15 + 30 90 80 fenoxaprop-P-ethyl Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl6.9% & mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-3 Application Lolium Lolium rate perenne perenne g of ai/haobserved calculated* Procarbazone- 30 30 sodium 15 0 Fenoxaprop-P- 60 0ethyl 30 0 Procarbazone- 30 + 60 70 30 sodium + 15 + 60 70 0fenoxaprop-P- 30 + 30 70 30 ethyl 15 + 30 50 0 Fenoxaprop-P-ethyl testedas Ralon ® super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Valuescalculated according to Colby

TABLE B-4 Application Amaranthus Amaranthus rate retroflexus retroflexusg of ai/ha observed calculated* Procarbazone- 30 90 sodium 15 80Fenoxaprop-P- 60 0 ethyl 30 0 Procarbazone- 30 + 60 95 90 sodium + 15 +60 95 80 fenoxaprop-P- 15 + 30 90 80 ethyl Fenoxaprop-P-ethyl tested asRalon ® super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Valuescalculated according to Colby

TABLE B-5 Application Galium Galium rate aparine aparine g of ai/haobserved calculated* Procarbazone- 60 40 sodium 30 30 15 20Fenoxaprop-P- 60 0 ethyl 30 0 15 0 Procarbazone- 60 + 60 80 40 sodium +30 + 60 60 30 fenoxaprop-P- 15 + 60 60 20 ethyl 60 + 30 80 40 30 + 30 6030 15 + 30 50 20 30 + 15 60 30 15 + 15 50 20 Fenoxaprop-P-ethyl testedas Ralon ® super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Valuescalculated according to Colby

TABLE B-6 Application Ipomoea Ipomoea rate hederacea hederacea g ofai/ha observed calculated* Procarbazone- 60 70 sodium 30 70 15 60Fenoxaprop-P- 60 0 ethyl 30 0 Procarbazone- 60 + 60 80 70 sodium + 30 +60 80 70 fenoxaprop-P- 15 + 60 80 60 ethyl 60 + 30 80 70 15 + 30 80 60Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-7 Application Solanum Solanum rate nigrum nigrum g of ai/haobserved calculated* Procarbazone- 30 70 sodium Fenoxaprop-P- 60 0 ethyl30 0 15 0 Procarbazone- 30 + 60 100 70 sodium + 30 + 30 90 70fenoxaprop-P- 30 + 15 90 70 ethyl Fenoxaprop-P-ethyl tested as Ralon ®super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Values calculatedaccording to Colby

TABLE B-8 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Procarbazone- 30 50 sodium 15 10 Fenoxaprop-P- 60 0ethyl 30 0 15 0 Fenoxaprop-P- 30 + 60 70 50 ethyl 15 + 60 70 10 30 + 3070 50 15 + 30 30 10 15 + 15 30 10 Fenoxaprop-P-ethyl tested as Ralon ®super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Values calculatedaccording to Colby

TABLE B-9 Application Xanthium Xanthium rate strumarium strumarium g ofai/ha observed calculated* Procarbazone- 30 70 sodium 15 60Fenoxaprop-P- 60 0 ethyl 30 0 Procarbazone- 30 + 60 90 70 sodium + 15 +60 80 60 fenoxaprop-P- 30 + 30 80 70 ethyl Fenoxaprop-P-ethyl tested asRalon ® super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Valuescalculated according to Colby

TABLE B-10 Application Bromus Bromus rate secalinus secalinus g of ai/haobserved calculated* Flucarbazone- 60 80 sodium 30 70 15 70Fenoxaprop-P- 60 0 ethyl 30 0 Flucarbazone- 15 + 60 90 70 sodium + 60 +30 90 80 fenoxaprop-P- 30 + 30 90 70 ethyl 15 + 30 90 70Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-11 Application Amaranthus Amaranthus rate retroflexusretroflexus g of ai/ha observed calculated* Flucarbazone- 30 90 sodium15 90 Fenoxaprop-P- 60 0 ethyl 30 0 Flucarbazone- 15 + 60 100 90sodium + 30 + 30 100 90 fenoxaprop-P- 15 + 30 100 90 ethylFenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-12 Application Chenopodium Chenopodium rate album album g ofai/ha observed calculated* Flucarbazone- 60 70 sodium 30 50 15 50Fenoxaprop-P- 60 0 ethyl 30 0 Flucarbazone- 60 + 60 90 70 sodium + 15 +60 80 50 fenoxaprop-P- 30 + 30 70 50 ethyl 15 + 30 70 50Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-13 Application Datura Datura rate strumarium strumarium g ofai/ha observed calculated* Flucarbazone- 60 80 sodium 15 70Fenoxaprop-P- 60 0 ethyl 30 0 Flucarbazone- 60 + 60 98 80 sodium + 15 +30 90 70 fenoxaprop-P- ethyl Fenoxaprop-P-ethyl tested as Ralon ® super(fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Values calculated accordingto Colby

TABLE B-14 Application Galium Galium rate aparine aparine g of ai/haobserved calculated* Flucarbazone- 60 0 sodium 30 0 15 0 Fenoxaprop-P-60 0 ethyl 30 0 Flucarbazone- 60 + 60 60 0 sodium + 30 + 60 50 0fenoxaprop-P- 15 + 60 50 0 ethyl 60 + 30 50 0 30 + 30 50 0 15 + 30 50 0Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-15 Application Polygonum Polygonum rate convolvolus convolvolusg of ai/ha observed calculated* Flucarbazone- 60 70 sodium 30 70 15 60Fenoxaprop-P- 60 0 ethyl 30 0 Flucarbazone- 60 + 60 95 70 sodium + 15 +60 90 60 fenoxaprop-P- 60 + 30 90 70 ethyl 30 + 30 90 70 15 + 30 90 60Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl 6.9% &mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-16 Application Stellaria Stellaria rate media media g off ai/haobserved calculated* Flucarbazone- 60 95 sodium 30 60 15 0 Fenoxaprop-P-60 0 ethyl 30 0 Flucarbazone- 60 + 60 100 95 sodium + 15 + 60 100 0fenoxaprop-P- 30 + 30 90 60 ethyl 15 + 30 50 0 Fenoxaprop-P-ethyl testedas Ralon ® super (fenoxaprop-P-ethyl 6.9% & mefenpyr 7.5%) *Valuescalculated according to Colby

TABLE B-17 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Flucarbazone- 15 60 sodium Fenoxaprop-P- 60 0 ethyl30 0 Flucarbazone- 15 + 60 90 60 sodium + 15 + 30 80 60 fenoxaprop-P-ethyl Fenoxaprop-P-ethyl tested as Ralon ® super (fenoxaprop-P-ethyl6.9% & mefenpyr 7.5%) *Values calculated according to Colby

TABLE B-18 Application Avena Avena rate fatua fatua g of ai/ha observedcalculated* Procarbazone- 30 90 sodium 15 70 Flufenacet 125 70Procarbazone- 30 + 125 100 97 sodium + 15 + 125 100 91 flufenacet*Values calculated according to Colby

TABLE B-19 Application Amaranthus Amaranthus rate retroflexusretroflexus g of ai/ha observed calculated* Procarbazone-  60 98 sodium 30 98  15 98 Flufenacet 125 0  60 0 Procarbazone-  60 + 125 100 98sodium +  30 + 125 100 98 flufenacet 60 + 60 100 98 30 + 60 100 98 15 +60 100 98 *Values calculated according to Colby

TABLE B-20 Application Polygonum Polygonum rate convolvolus convolvolusg of ai/ha observed calculated* Procarbazone-  60 0 sodium Flufenacet125 0 Procarbazone- 60 + 125 40 0 sodium + flufenacet *Values calculatedaccording to Colby

TABLE B-21 Application Alopecurus Alopecurus rate myosuroidesmyosuroides g of ai/ha observed calculated* Procarbazone- 60 90 sodium30 80 15 80 Cinidon-ethyl 15 0  8 0 Procarbazone- 60 + 15 95 90 sodium +30 + 15 99 80 cinidon-ethyl 60 + 8  95 90 30 + 8  95 80 15 + 8  90 80*Values calculated according to Colby

TABLE B-22 Application rate Avena fatua Avena fatua g of ai/ha observedcalculated* Procarbazone- 60 60 sodium 30 50 15 50 Cinidon-ethyl 15 10 8 0 Procarbazone- 60 + 15 90 64 sodium + 30 + 15 70 55 cinidon-ethyl15 + 15 80 55 60 + 8  70 60 30 + 8  90 50 15 + 8  80 50 *Valuescalculated according to Colby

TABLE B-23 Application Bromus Bromus rate secalinus secalinus g of ai/haobserved calculated* Procarbazone- 60 90 sodium 30 80 15 70Cinidon-ethyl 15 20  8 0 Procarbazone- 60 + 15 99 92 sodium + 30 + 15 9084 cinidon-ethyl 15 + 15 80 76 60 + 8  95 90 30 + 8  95 80 15 + 8  80 70*Values calculated according to Colby

TABLE B-24 Application Cyperus Cyperus rate esculentus esculentus g ofai/ha observed calculated* Procarbazone- 30 80 sodium 15 70Cinidon-ethyl 15 20  8 0 Procarbazone- 30 + 15 95 84 sodium + 30 + 8  9080 cinidon-ethyl 15 + 8  95 70 *Values calculated according to Colby

TABLE B-25 Application Echinochloa Echinochloa rate crus-gallicrus-galli g of ai/ha observed calculated* Procarbazone- 60 90 sodium 3090 Cinidon-ethyl 15 0  8 0 Procarbazone- 60 + 15 99 90 sodium + 30 + 8 100 90 cinidon-ethyl *Values calculated according to Colby

TABLE B-26 Application Eriochloa Eriochloa rate villosa villosa g ofai/ha observed calculated* Procarbazone- 15 0 sodium Cinidon-ethyl 15 30Procarbazone- 15 + 15 80 30 sodium + cinidon-ethyl *Values calculatedaccording to Colby

TABLE B-27 Application Lolium Lolium rate perenne perenne g of ai/haobserved calculated* Procarbazone- 30 20 sodium Cinidon-ethyl  8 0Procarbazone- 30 + 8 70 20 sodium + cinidon-ethyl *Values calculatedaccording to Colby

TABLE B-28 Application rate Cassia tora Cassia tora g of ai/ha observedcalculated* Procarbazone- 30 0 sodium Cinidon-ethyl 15 95 Procarbazone-30 + 15 100 95 sodium + cinidon-ethyl *Values calculated according toColby

TABLE B-29 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Procarbazone- 60 80 sodium 30 70 15 50Cinidon-ethyl 15 30  8 0 Procarbazone- 60 + 15 95 86 sodium + 30 + 15 9079 cinidon-ethyl 15 + 15 90 65 60 + 8  90 80 30 + 8  80 70 15 + 8  60 50*Values calculated according to Colby

TABLE B-30 Application rate Avena fatua Avena fatua g of ai/ha observedcalculated* Procarbazone- 60 60 sodium 30 50 Florasulam 15 50  8 30Procarbazone- 60 + 15 90 80 sodium + 30 + 8  80 65 florasulam *Valuescalculated according to Colby

TABLE B-31 Application Lolium Lolium rate perenne perenne g of ai/haobserved calculated* Procarbazone- 60 50 sodium 30 20 Florasulam 15 30 8 20 Procarbazone- 60 + 15 70 65 sodium + 30 + 15 70 44 florasulam 30 +8  60 36 *Values calculated according to Colby

TABLE B-32 Application rate Cassia tora Cassia tora g of ai/ha observedcalculated* Procarbazone- 60 30 sodium 30 0 Florasulam 15 95  8 90Procarbazone- 60 + 15 100 96.5 sodium + 30 + 8  95 90 florasulam *Valuescalculated according to Colby

TABLE B-33 Application Polygonum Polygonum rate convolvolus convolvolusg of ai/ha observed calculated* Procarbazone- 60 0 sodium 30 0Florasulam 15 95  8 95 Procarbazone- 30 + 15 99 95 sodium + 60 + 8  9995 florasulam 30 + 8  99 95 *Values calculated according to Colby

TABLE B-34 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Procarbazone- 15 50 sodium Florasulam  8 70Procarbazone- 15 + 8 90 85 sodium + florasulam *Values calculatedaccording to Colby

TABLE B-35 Application Alopecurus Alopecurus rate myosuroidesmyosuroides g of ai/ha observed calculated* Flucarbazone- 60 70 sodium30 70 15 70 Florasulam  4 0  2 0 Flucarbazone- 15 + 4 90 70 sodium +60 + 2 95 70 florasulam 30 + 2 90 70 *Values calculated according toColby

TABLE B-36 Application rate Avena fatua Avena fatua g of ai/ha observedcalculated* Flucarbazone- 60 90 sodium 30 90 15 80 Florasulam  4 10  2 0Flucarbazone- 60 + 4 95 91 sodium + 30 + 4 95 91 florasulam 15 + 4 95 8260 + 2 98 90 30 + 2 98 90 15 + 2 90 80 *Values calculated according toColby

TABLE B-37 Application Bromus Bromus rate secalinus secalinus g of ai/haobserved calculated* Flucarbazone- 60 90 sodium 30 90 15 70 Florasulam 4 0  2 0 Flucarbazone- 60 + 4 98 90 sodium + 30 + 4 100 90 florasulam15 + 4 90 70 60 + 2 100 90 15 + 2 80 70 *Values calculated according toColby

TABLE B-38 Application Digitaria Digitaria rate sanguinalis sanguinalisg of ai/ha observed calculated* Flucarbazone- 60 20 sodium 30 20Florasulam  4 0  2 0 Flucarbazone- 60 + 4 60 20 sodium + 30 + 4 60 20florasulam 60 + 2 80 20 *Values calculated according to Colby

TABLE B-39 Application Echinochloa Echinochloa rate crus-gallicrus-galli g of ai/ha observed calculated* Flucarbazone- 60 90 sodium 1550 Florasulam  4 40  2 10 Flucarbazone- 60 + 4 98 94 sodium + 15 + 4 8070 florasulam 60 + 2 100 91 15 + 2 70 55 *Values calculated according toColby

TABLE B-40 Application Lolium Lolium rate perenne perenne g of ai/haobserved calculated* Flucarbazone- 60 90 sodium 30 90 15 80 Florasulam 4 0  2 0 Flucarbazone- 60 + 4 95 90 sodium + 30 + 4 95 90 florasulam15 + 4 90 80 60 + 2 100 90 30 + 2 98 90 *Values calculated according toColby

TABLE B-41 Application Abutilon Abutilon rate theophrasti theophrasti gof ai/ha observed calculated* Flucarbazone- 60 0 sodium 30 0 15 0Florasulam  4 30  2 20 Flucarbazone- 60 + 4 60 30 sodium + 30 + 4 60 30florasulam 15 + 4 60 30 60 + 2 70 20 30 + 2 70 20 *Values calculatedaccording to Colby

TABLE B-42 Application Amaranthus Amaranthus rate retroflexusretroflexus g of ai/ha observed calculated* Flucarbazone- 60 90 sodium30 90 15 90 Florasulam  4 70  2 70 Flucarbazone- 60 + 4 100 97 sodium +30 + 4 100 97 florasulam 15 + 4 100 97 60 + 2 100 97 30 + 2 100 97*Values calculated according to Colby

TABLE B-43 Application Galium Galium rate aparine aparine g of ai/haobserved calculated* Flucarbazone- 60 0 sodium 30 0 15 0 Florasulam  450  2 50 Flucarbazone- 60 + 4 70 50 sodium + 30 + 4 70 50 florasulam15 + 4 60 50 60 + 2 90 50 *Values calculated according to Colby

TABLE B-44 Application Matricaria Matricaria rate inodora inodora g ofai/ha observed calculated* Flucarbazone- 60 20 sodium Florasulam  2 70Flucarbazone- 60 + 2 98 76 sodium + florasulam *Values calculatedaccording to Colby

TABLE B-45 Application Veronica Veronica rate persicaria persicaria g ofai/ha observed calculated* Flucarbazone- 60 0 sodium Florasulam  4 0  20 Flucarbazone- 60 + 4 40 0 sodium + 60 + 2 70 0 florasulam *Valuescalculated according to Colby

TABLE B-46 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Flucarbazone- 60 50 sodium 30 50 15 50 Florasulam 4 0  2 0 Flucarbazone- 60 + 4 100 50 sodium + 30 + 4 80 50 florasulam15 + 4 80 50 60 + 2 98 50 30 + 2 90 50 *Values calculated according toColby

TABLE B-47 Application Xanthium Xanthium rate strumarium strumarium g ofai/ha observed calculated* Flucarbazone- 60 60 sodium 30 40 15 20Florasulam  4 50  2 40 Flucarbazone- 30 + 4 80 70 sodium + 15 + 4 70 60florasulam 60 + 2 80 76 30 + 2 70 64 15 + 2 70 52 *Values calculatedaccording to Colby

TABLE B-48 Application rate Cassia tora Cassia tora g of ai/ha observedcalculated* Procarbazone- 60 50 sodium 30 50 15 50 Amicarbazone 30 40Procarbazone- 60 + 30 100 70 sodium + 30 + 30 98 70 amicarbazone 15 + 3098 70 *Values calculated according to Colby

TABLE B-49 Application Stellaria Stellaria rate media media g of ai/haobserved calculated* Procarbazone- 60 70 sodium 30 60 15 50 Amicarbazone60 80 Procarbazone- 60 + 60 100 94 sodium + 30 + 60 100 92 amicarbazone15 + 60 100 90 *Values calculated according to Colby

TABLE B-50 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Procarbazone- 15 60 sodium Amicarbazone 30 70Procarbazone- 15 + 30 100 88 sodium + amicarbazone *Values calculatedaccording to Colby

TABLE B-51 Application Xanthium Xanthium rate strumarium strumarium g ofai/ha observed calculated* Procarbazone- 60 60 sodium 30 60 Amicarbazone30 80 Procarbazone- 60 + 30 98 92 sodium + 30 + 30 98 92 amicarbazone*Values calculated according to Colby

TABLE B-52 Application Abutilon Abutilon rate theophrasti theophrasti gof ai/ha observed calculated* Procarbazone- 60 60 sodium Amicarbazone 3080 Procarbazone- 60 + 30 98 92 sodium + amicarbazone *Values calculatedaccording to Colby

TABLE B-53 Application Eriochloa Eriochloa rate villosa villosa g ofai/ha observed calculated* Flucarbazone-  60 70 sodium Amicarbazone 12570 Flucarbazone- 60 + 125 100 91 sodium + amicarbazone *Valuescalculated according to Colby

TABLE B-54 Application Viola Viola rate arvensis arvensis g of ai/haobserved calculated* Flucarbazone- 15 80 sodium Amicarbazone 30 70Flucarbazone- 15 + 30 100 94 sodium + amicarbazone *Values calculatedaccording to Colby

TABLE B-55 Application rate Cassia tora Cassia tora G of ai/ha observedcalculated* Flucarbazone- 60 50 sodium 30 50 15 50 Amicarbazone 30 40Flucarbazone- 60 + 30 100 70 sodium + 30 + 30 100 70 amicarbazone 15 +30 100 70 *Values calculated according to Colby

TABLE B-56 Application Matricaria Matricaria rate inodora inodora g offai/ha observed calculated* Flucarbazone- 60 60 sodium 30 60 15 20Amicarbazone 30 60 Flucarbazone- 60 + 30 98 84 sodium + 30 + 30 90 84amicarbazone 15 + 30 90 68 *Values calculated according to Colby

TABLE B-57 Application rate Avena fatua Avena fatua g of ai/ha observedcalculated* Flucarbazone- 60 70 sodium 30 70 15 70 Amicarbazone 30 0flucarbazone- 60 + 30 98 70 sodium + 30 + 30 95 70 amicarbazone 15 + 3080 70 *Values calculated according to Colby

TABLE B-58 Application rate Avena fatua Avena fatua g of ai/ha observedcalculated* Procarbazone- 15 80 sodium Iodosufuron  8 70 Procarbazone-15 + 8 98 94 sodium + iodosulfuron Iodosulfuron tested as Hussar ®(iodosulfuron 5% & mefenpyr 15%) *Values calculated according to Colby

TABLE B-59 Application Bromus Bromus rate secalinus secalinus g of ai/haobserved calculated* Procarbazone- 30 90 sodium 15 90 Iodosulfuron  8 0 4 0  2 0 Procarbazone- 30 + 8 95 90 sodium + 30 + 4 95 90 iodosulfuron15 + 4 95 90 30 + 2 95 90 Iodosulfuron tested as Hussar ® (iodosulfuron5% & mefenpyr 15%) *Values calculated according to Colby

TABLE B-60 Application Setaria Setaria rate viridis viridis g of ai/haobserved calculated* Procarbazone- 60 20 sodium 30 0 15 0 Iodosulfuron 4 0 Procarbazone- 60 + 4 60 20 sodium + 30 + 4 40 0 iodosulfuron 15 + 430 0 Iodosulfuron tested as Hussar ® (iodosulfuron 5% & mefenpyr 15%)*Values calculated according to Colby

TABLE B-61 Application Polygonum Polygonum rate convolvolus convolvolusg of ai/ha observed calculated* Procarbazone- 60 0 sodium 30 0 15 0Iodosulfuron 2 80 Procarbazone- 60 + 2 100 80 sodium + 30 + 2 95 80iodosulfuron 15 + 2 90 80 Iodosulfuron tested as Hussar ® (iodosulfuron5% & mefenpyr 15%) *Values calculated according to Colby

TABLE B-62 Application rate Avena fatua Avena fatua g of ai/ha observedcalculated* Flucarbazone- 15 80 sodium Iodosulfuron 2 10 Flucarbazone-15 + 2 95 82 sodium + iodosulfuron Iodosulfuron tested as Hussar ®(iodosulfuron 5% & mefenpyr 15%) *Values calculated according to Colby

TABLE B-63 Application Echinochloa Echinochloa rate crus-gallicrus-galli g of ai/ha observed calculated* Flucarbazone- 60 90 sodium 3070 15 60 Iodosulfuron 2 20 Flucarbazone- 60 + 2 98 92 sodium + 30 + 2 9576 iodosulfuron 15 + 2 90 68 Iodosulfuron tested as Hussar ®(iodosulfuron 5% & mefenpyr 15%) *Values calculated according to Colby

TABLE B-64 Application rate Cassia tora Cassia tora g of ai/ha observedcalculated* Flucarbazone- 15 0 sodium Iodosulfuron 8 80 Flucarbazone-15 + 8 90 80 sodium + iodosulfuron Iodosulfuron tested as Hussar ®(iodosulfuron 5% & mefenpyr 15%) *Values calculated according to Colby

1. A composition comprising an active compound combination of: (a) anarylsulphonylaminocarbonyltriazolinone selected from the groupconsisting of the compound2-(2-methoxycarbonyl-phenysulphonylaminocarbonyl)-4-methyl-5-n-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(procarbazone or propoxicarbazone), the compound2-(2-trifluoromethoxy-phenysulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one(flucarbazone) and a sodium salt of these two compounds(propoxicarbazone-sodium or flucarbazone-sodium) (“active compounds ofgroup 1”) and (b) one to three compounds selected from a second group ofherbicides comprising the active compounds listed below: ethyl2-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl-phenyl]-2-propanoate(cinidon-ethyl),N-(2,6-difluoro-phenyl)-8-fluoro-5-methoxy-[1,2,4]-triazolo-[1,5-c]-pyrimidine-2-sulphonamide(florasulam),(R)-2-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy)-phenoxy]-propanoicacid (methyl ester, 2-ethoxy-ethyl ester, butyl ester) (haloxyfop,-methyl, -P-methyl, -ethoxyethyl, -butyl),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N′-(5-iodo-2-methoxycarbonyl-phenylsulphonyl)-ureasodium salt (iodosulfuron-methyl-sodium), methyl2-[[[[(4,6-dimethoxy-2-pyrimidinyl)-amino]-carbonyl]-amino]-sulphonyl]-4-[[(methylsulphonyl)-amino]methyl]-benzoate(mesosulfuron), (“active compounds of group 2”), and optionally (c) acompound which improves crop plant compatibility selected from the groupof compounds below: 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane,1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one(dicyclonon), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine(benoxacor), 1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate(cloquintocet-mexyl),3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron),α-(cyanomethoximino)-phenylacetonitrile (cyometrinil),2,4-dichloro-phenoxy acetic acid (2,4-D),1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron),3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethylpiperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide,2,2-dichloro-N,N-di-2-propenyl acetamide (dichlormid),4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl1-(2,4-dichloro-phenyl)-5-trichloro-methyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl, phenyl-methyl2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine(furilazole,), ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate(isoxadifen-ethyl),diethyl-1-(2,4-dichloro-phenyl)4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane,1,8-naphthalic anhydride,α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide,3-dichloroacetyl-2,2-dimethyl-oxazolidine,3-dichloroacetyl-2,2,5-trimethyl-oxazolidine, methyl1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate,1,3-dimethyl-but-1-yl 5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinolin-8-oxy-acetate,ethyl 5-chloro-quinolin-8-oxy-acetate, allyl5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl5-chloro-quinolin-8-oxy-acetate, diethyl5-chloro-quinolin-8-oxy-malonate, diallyl5-chloro-quinolin-8-oxy-malonate, diethyl5-chloro-quinolin-8-oxy-malonate, 2-(4-carboxy-chroman-4-yl)-aceticacid, 3,3′-dimethyl-4-methoxy-benzophenone,1-bromo-4-chloromethylsulphonyl-benzene,N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide,N-(2-methoxy-5-methyl-benzoyl)-4,(cyclopropylaminocarbonyl)-benzene-sulphonamide,N-cyclopropyl-4-[(2-methoxy-5-methyl-benzoyl)-amino-sulphonyl]benzamide,“active compounds of group 3”) excluding mixtures of flucarbazone orflucarbazone-sodium with cinidon-ethyl.
 2. A method for controllingundesirable plants comprising the step of allowing a compositionaccording to claim 1 to act on the undesirable plants and/or theirhabitat.
 3. A process for preparing a herbicidal composition, comprisingmixing a composition according to claim 1 with one or more surfactantsand/or extenders.
 4. A composition according to claim 1 wherein thecompound which improves crop plant compatibility (component (c)) isselected from the group of active compounds consisting of:1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl) anddiethyl1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl).
 5. A composition according to claim 1 wherein from0.01 to 1000 parts by weight of the active compound(s) from the secondgroup of herbicides (component (b)) are used per part by weight ofactive compound of the formula (I).
 6. A composition according to claim1 wherein from 0.001 to 1000 parts by weight of the active compoundwhich improves crop plant compatibility (component (c)) is used per partby weight of active compound of the formula (I) or its mixtures withactive compounds from the second group of herbicides (component (b)).